N-(6-苯基吡啶-2-基)苯甲酰胺 | 1044239-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: N-(6-苯基吡啶-2-基)苯甲酰胺
• 英文名称: N-(6-phenylpyridin-2-yl)benzamide
• CAS: 1044239-11-3
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: DEHCNDLHYIPCMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(6-苯基吡啶-2-基)苯甲酰胺 在 双(乙腈)氯化钯(II) 、 氧气 、 丙醛 作用下， 以 1,2-二氯乙烷 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 以65%的产率得到
  参考文献：
  名称：

  醛自氧化诱导钯催化的2-芳基吡啶有氧直接C（sp2）-H羟基化

  摘要：

  本文中，我们介绍了使用分子氧（O 2）作为唯一氧化剂的Pd催化2-芳基吡啶的直接C–H羟基化反应。该方法的关键方面包括：（a）用无毒且廉价的醛活化分子氧；（b）原位产生的酰基过氧自由基与钯催化的有效结合；（c）方便的操作条件。基于一系列对照实验中获得的结果，涉及Pd II / Pd IV催化循环的转化。此外，该方法可容易地以良好的分离产率获得广泛范围的取代的2-（吡啶-2-基）苯酚。

  DOI：

  10.1021/acscatal.6b01539
• 作为产物：
  描述：

  6-苯基吡啶-2-胺 、 苯甲酰氯 在 吡啶 作用下， 反应 2.0h， 以64%的产率得到N-(6-苯基吡啶-2-基)苯甲酰胺
  参考文献：
  名称：

  False Positives in a Reporter Gene Assay: Identification and Synthesis of Substituted N-Pyridin-2-ylbenzamides as Competitive Inhibitors of Firefly Luciferase

  摘要：

  Luciferase reporter-gene assays are a commonly used technique in high-throughput screening campaigns. In this study, we report on a luciferase inhibitor (1), which emerged from an antagonistic G protein-coupled receptor luciferase reporter-gene assay screen. Instead of displaying receptor activity, compound I was shown to potently inhibit luciferase in an in vitro enzymatic assay with an IC50 value of 1.7 +/- 0.1 mu M. In addition, 1 was a competitive inhibitor with respect to the substrate luciferin. A database search yielded another inhibitor (3) with a similar N-pyridin-2-ylbenzamide core. Subsequently, several analogues were prepared to investigate the structure-activity relationships of these luciferase inhibitors. This yielded the most potent inhibitor of this series (6) with an IC50 value of 0.069 +/- 0.01 mu M. Further molecular modeling studies suggested that 6 can be accommodated in the luciferin binding site. This paper is meant to alert users of luciferase reporter-gene assays for possible false positive hits including highly "druglike" molecules due to direct luciferase inhibition.

  DOI：

  10.1021/jm8004509

文献信息

• Aerobic Direct C(sp2)-H Hydroxylation of 2-Arylpyridines by Palladium Catalysis Induced with Aldehyde Auto-Oxidation
  作者：Prasenjit Das、Debajyoti Saha、Dibyajyoti Saha、Joyram Guin

  DOI：10.1021/acscatal.6b01539

  日期：2016.9.2

  Herein we present a Pd-catalyzed direct C–H hydroxylation of 2-arylpyridines using molecular oxygen (O2) as the sole oxidant. The key aspects of the method include: (a) the activation of molecular oxygen with a nontoxic and inexpensive aldehyde; (b) an efficient association of the in situ-generated acyl peroxo radical with palladium catalysis; and (c) convenient operating conditions. On the basis of

  本文中，我们介绍了使用分子氧（O 2）作为唯一氧化剂的Pd催化2-芳基吡啶的直接C–H羟基化反应。该方法的关键方面包括：（a）用无毒且廉价的醛活化分子氧；（b）原位产生的酰基过氧自由基与钯催化的有效结合；（c）方便的操作条件。基于一系列对照实验中获得的结果，涉及Pd II / Pd IV催化循环的转化。此外，该方法可容易地以良好的分离产率获得广泛范围的取代的2-（吡啶-2-基）苯酚。
• False Positives in a Reporter Gene Assay: Identification and Synthesis of Substituted <i>N</i>-Pyridin-2-ylbenzamides as Competitive Inhibitors of Firefly Luciferase
  作者：Laura H. Heitman、Jacobus P. D. van Veldhoven、Annelien M. Zweemer、Kai Ye、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm8004509

  日期：2008.8.1

  Luciferase reporter-gene assays are a commonly used technique in high-throughput screening campaigns. In this study, we report on a luciferase inhibitor (1), which emerged from an antagonistic G protein-coupled receptor luciferase reporter-gene assay screen. Instead of displaying receptor activity, compound I was shown to potently inhibit luciferase in an in vitro enzymatic assay with an IC50 value of 1.7 +/- 0.1 mu M. In addition, 1 was a competitive inhibitor with respect to the substrate luciferin. A database search yielded another inhibitor (3) with a similar N-pyridin-2-ylbenzamide core. Subsequently, several analogues were prepared to investigate the structure-activity relationships of these luciferase inhibitors. This yielded the most potent inhibitor of this series (6) with an IC50 value of 0.069 +/- 0.01 mu M. Further molecular modeling studies suggested that 6 can be accommodated in the luciferin binding site. This paper is meant to alert users of luciferase reporter-gene assays for possible false positive hits including highly "druglike" molecules due to direct luciferase inhibition.